NO742321L - - Google Patents
Info
- Publication number
- NO742321L NO742321L NO742321A NO742321A NO742321L NO 742321 L NO742321 L NO 742321L NO 742321 A NO742321 A NO 742321A NO 742321 A NO742321 A NO 742321A NO 742321 L NO742321 L NO 742321L
- Authority
- NO
- Norway
- Prior art keywords
- ferric
- acid
- test strip
- salt
- phenylketone
- Prior art date
Links
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002250 absorbent Substances 0.000 claims description 11
- 230000002745 absorbent Effects 0.000 claims description 11
- 239000000797 iron chelating agent Substances 0.000 claims description 11
- 229940075525 iron chelating agent Drugs 0.000 claims description 11
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 10
- 238000001514 detection method Methods 0.000 claims description 10
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkali metal salts Chemical class 0.000 claims description 6
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 claims description 6
- FPFSGDXIBUDDKZ-UHFFFAOYSA-N 3-decyl-2-hydroxycyclopent-2-en-1-one Chemical compound CCCCCCCCCCC1=C(O)C(=O)CC1 FPFSGDXIBUDDKZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 239000002738 chelating agent Substances 0.000 claims description 4
- FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 claims description 4
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 claims description 4
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 4
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 4
- 239000005955 Ferric phosphate Substances 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 claims description 3
- 229940032958 ferric phosphate Drugs 0.000 claims description 3
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 claims description 3
- 229910000399 iron(III) phosphate Inorganic materials 0.000 claims description 3
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 claims description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 3
- 229960003330 pentetic acid Drugs 0.000 claims description 3
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 229960001484 edetic acid Drugs 0.000 claims 2
- 229960002413 ferric citrate Drugs 0.000 claims 2
- NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 claims 2
- 229940123150 Chelating agent Drugs 0.000 claims 1
- 201000011252 Phenylketonuria Diseases 0.000 description 14
- 210000002700 urine Anatomy 0.000 description 13
- 229920002678 cellulose Polymers 0.000 description 10
- 239000001913 cellulose Substances 0.000 description 10
- 210000001124 body fluid Anatomy 0.000 description 9
- 239000010839 body fluid Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 6
- JVIPLYCGEZUBIO-UHFFFAOYSA-N 2-(4-fluorophenyl)-1,3-dioxoisoindole-5-carboxylic acid Chemical compound O=C1C2=CC(C(=O)O)=CC=C2C(=O)N1C1=CC=C(F)C=C1 JVIPLYCGEZUBIO-UHFFFAOYSA-N 0.000 description 5
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 5
- 229920001425 Diethylaminoethyl cellulose Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 3
- 210000002381 plasma Anatomy 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FCKYPQBAHLOOJQ-UHFFFAOYSA-N Cyclohexane-1,2-diaminetetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)C1CCCCC1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UHFFFAOYSA-N 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000013399 early diagnosis Methods 0.000 description 2
- 229910001447 ferric ion Inorganic materials 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 208000029767 Congenital, Hereditary, and Neonatal Diseases and Abnormalities Diseases 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 208000036364 Normal newborn Diseases 0.000 description 1
- 108010069013 Phenylalanine Hydroxylase Proteins 0.000 description 1
- 102100038223 Phenylalanine-4-hydroxylase Human genes 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 241000736772 Uria Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000016097 disease of metabolism Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 230000036630 mental development Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 208000024335 physical disease Diseases 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000012764 semi-quantitative analysis Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/64—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving ketones
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/200833—Carbonyl, ether, aldehyde or ketone containing
Description
"Provestrimmel for påvisning av "Test strip for the detection of
fenylketon-partikler".phenylketone particles".
Foreliggende oppfinnelse vedrører en prøvestrimmel for påvisning av fenylketon-legemer i kroppsvæskene og en sammensetning derfor. Mer spesielt vedrører den foreliggende oppfinnelse en prøvestrimmel for påvisning av fenylketon-legemer i kroppsvæskene, spesielt i urinen, omfattende et absorberende materiale, et ferri«salt og et jern-chelaterende middel, og en'sammensetning derfor omfattende et ferri-salt og et jern-chelaterende middel. The present invention relates to a test strip for the detection of phenylketone bodies in body fluids and a composition therefore. More particularly, the present invention relates to a test strip for the detection of phenylketone bodies in the body fluids, especially in the urine, comprising an absorbent material, a ferric salt and an iron chelating agent, and a composition therefore comprising a ferric salt and an iron -chelating agent.
Nærværet av fenylketon-legemer som f.eks. fenyl«pyrodruesyre i kroppsvæskene, spesielt i urinen, er et tegn på fenylketon« uria som er en medfødt forstyrrelse av fenylalaninlrietabolismen i levende organismer. Denne alvorlige metaboliske sykdom er grunnen til medale forstyrrelser, uheldig mental utvikling, øket pigmentering, hudsykdommer etc. Normal metabolisme av. fenylalanin til tyrosin iakttas i normale nyfødte barn. Da pasienter med fenylketonura imidlertid mangler fenylalanin-hydroksylase, oppsamles fenylketon-legemer i de levende organismer, og utskilles i urinen i stor mengde'» Påvisning av fenylketon-legemer som f.eks. fenyldruesyre i kroppsvæskene (f.eks. urinen,serum, plasma) utgjør således en diagnose på fenylketonuria. Da fenylketonuria kan helbredes ved å be-grense opptakningen av fenylalanin i en diett kreves tidlig diagnose av denne sykdom. The presence of phenylketone bodies such as phenyl«pyruvic acid in the body fluids, especially in the urine, is a sign of phenylketon«uria which is a congenital disorder of phenylalanine metabolism in living organisms. This serious metabolic disease is the reason for mental disorders, poor mental development, increased pigmentation, skin diseases etc. Normal metabolism of. phenylalanine to tyrosine is observed in normal newborns. As patients with phenylketonuria, however, lack phenylalanine hydroxylase, phenylketone bodies accumulate in the living organisms, and are excreted in the urine in large quantities.'' Detection of phenylketone bodies such as phenylgravic acid in body fluids (e.g. urine, serum, plasma) thus constitutes a diagnosis of phenylketonuria. As phenylketonuria can be cured by limiting the intake of phenylalanine in a diet, early diagnosis of this disease is required.
Det er kjent at en prøvestrimmel som inneholder ferriklorid alene eller ferri-ammoniumsulfat alene som aktivt komponent kan anvendes for diagnose av fenylketonuria, men denne prøve-strimmel er ustabil og dens følsomhet overfor fenylketon-legemer er ikke høy. Man har videre foreslått en diagnostisk sammensetning for fenylketonuria, omfattende et ferrisalt, en organisk syre og et fosfat-komplekserende middel. Som et eksempel på en kdnversiell tilgjengelig prøvestrimmel anvendt for slik påvisning kan nevnes et prø^e«. papir omfattende ferri-ammoniumsulfat og natriumsyklamat, og en prøvestrimmel omfattende ferriammoniumsulfat, magnesiumsulfat og borsyre. It is known that a test strip containing ferric chloride alone or ferric ammonium sulfate alone as active component can be used for the diagnosis of phenylketonuria, but this test strip is unstable and its sensitivity to phenylketone bodies is not high. A diagnostic composition for phenylketonuria has also been proposed, comprising a ferric salt, an organic acid and a phosphate-complexing agent. As an example of a universally available test strip used for such detection, a sample can be mentioned. paper comprising ferric ammonium sulphate and sodium cyclamate, and a test strip comprising ferric ammonium sulphate, magnesium sulphate and boric acid.
Når imidlertid disse prøvestrimler bringes i kontakt med en bleie som er fuktig av urin, blir bleien farget og skitten med reagensen som inneholdes i prøvestrimmelen, og den farge som dannes av prøvestrimmelen er ikke jevn og har tendens til hurtig å blekne. I motsetning hertil, har prøvestrimlene for fenylketonuria i henhold til den foreliggende oppfinnelse ikke de overnevnte mangler, og de fremviser en rekke fordelaktige trekk som følger: (l) resultatet av prøven er pålitelig, (2) semikvantitativ analyse er mulig, { J>) prøvestrimmelen kan påvise fenylketon-legemer i urinen ved"en konsentrasjon på mer enn 10 mg/lOOml, (4) tydelig, stabil og jevn farge (gul(normal) blågrønn(unormal)) kommer frem med en gang, og bestemne Isen kan gjøres hurtig, (5) den farge som dannes ved prøven blekner ikke hurtig, og (6)"påvisningen av fenylketon-legemer er mulig enndog på en bleie"som er fuktig med urin uten å tilsmusse denne. However, when these test strips are brought into contact with a diaper moistened with urine, the diaper becomes stained and soiled with the reagent contained in the test strip, and the color produced by the test strip is not uniform and tends to fade quickly. In contrast, the test strips for phenylketonuria according to the present invention do not have the above-mentioned shortcomings, and they exhibit a number of advantageous features as follows: (1) the result of the test is reliable, (2) semi-quantitative analysis is possible, {J>) the test strip can detect phenylketone bodies in the urine at a concentration of more than 10 mg/lOOml, (4) clear, stable and uniform color (yellow(normal) blue-green(abnormal)) appears at once, and determine the Isen can be made rapid, (5) the color produced by the test does not fade rapidly, and (6) "the detection of phenylketone bodies is possible even on a diaper" that is wet with urine without soiling it.
Prøvestrimlene i henhold til oppfinnelsen kan dog således anvendes lett, hurtig og nøyaktig for tidlig diagnose av fenylketon-legemer i kroppsvæskene, spesielt i urinen. Sammensetningene i henhold til oppfinnelsen viser visse fordelaktige trekk som nevnt ovenfor. The test strips according to the invention can thus be used easily, quickly and accurately for early diagnosis of phenylketone bodies in the body fluids, especially in the urine. The compositions according to the invention show certain advantageous features as mentioned above.
Prøvestrimlene for fenylketonuria og sammensetningene for dette' skal i, det følgende beskrives mer detaljert. The test strips for phenylketonuria and the compositions for this will be described in more detail below.
For å fremstille prøvestrimmelen i henhold til den foreliggende oppfinnelse, oppløses først et ferrisalt og et jern-ohelater-ende middel i et passende løsningsmiddel til å gi en gulaktig løsning. Et absorberende materiale som for eksempel papir, tekstilduk, eller en trepinne dyppes ned i denne oppløsning omtrent ved romtemperatur, og deretter tørres det neddyppete absorberende materiale i luften eller ved en temperatur på To prepare the test strip according to the present invention, a ferric salt and an iron-chelating agent are first dissolved in a suitable solvent to give a yellowish solution. An absorbent material such as paper, textile cloth or a wooden stick is dipped into this solution at approximately room temperature, and then the dipped absorbent material is dried in the air or at a temperature of
fra romtemperatur til 50°C for å gi den ønskede prøvestrimmel. Som en alternativ metode kan prøvestrimmelen i henhold til oppfinnelsen fremstilles ved å dyppe et absorberende materiale ned i en løsning inneholdende alle de nødvendige komponenter. Det bemerkes at rekkefølgen for tilsetningen av de nevnte komponenter ikke er av særlig viktighet. Et overflateaktivt middel som f.eks. polyetylenglykol 4000 kan tilsettes til den impregnerende løsning for stabilisering av de aktive forbindelser. Selvom selve- løsningen inneholdende de aktive komponenter kan anvendes for påvisning av fenylketon-legemer kan en prøvestrim-mel anvendes med fordel, med hensyn til lagring, stabilitet og håndtering. from room temperature to 50°C to give the desired test strip. As an alternative method, the test strip according to the invention can be produced by dipping an absorbent material into a solution containing all the necessary components. It is noted that the order in which the aforementioned components are added is not of particular importance. A surfactant such as e.g. polyethylene glycol 4000 can be added to the impregnating solution to stabilize the active compounds. Although the self-solution containing the active components can be used for the detection of phenylketone bodies, a test strip can be used with advantage, with regard to storage, stability and handling.
Som ferrisalter kan nevnes organiske eller uorganiske ferrisalter, som for eksempel ferriklorid, ferribromid, ferrifluorid, ferrisulfat, ferriammoniumsulfat, ferrinitrat, ferri fosfat og ferrioxalat. Det jern-chelaterende middel kan være en forbindelse som er i stand til å danne en chelatforbindelse med jernet og som ikke inhiberer fargereaksjonen. Slike chelaterende midler er foretrukket etylendiamintetraeddiksyre, nitriloeddiksyre, l,2«syklohexandiamintetraeddiksyre,glykoleterdiamintetraeddiksyre, dietylentriaminpentaeddiksyre, trietanolamin, dietanolamin, diacetylmonooxim, og uorganiske salter derav (f.eks. alkalimetallsalter). Blant disse forbindelser foretrekkes det spesielt å anvende etylendiamintetraeddiksyre og et alkalimetallsalt derav (f.eks. natrium-eller kalium-saltet). Disse jern-chelaterendé midler koordinerer med ferri-ioner sammen med fenylketon-legemer til å gi en farget chelatforbindelse som bidrar meget til stabiliteringen av ferri-ionet. Det antas således at tydelig og stabil farge dannes uten den uønskede dannelse av ferri-hydroksyd som et bunnfall. Det chelaterende middel kan også. maskere forskjellige metallioher i kroppsvæskene som uønsket påvirker fargereaksjonen. Som et resultat dannes en meget stabil farge med sterkt intensitet med farge-reaksjonen. Organic or inorganic ferric salts can be mentioned as ferric salts, such as ferric chloride, ferric bromide, ferric fluoride, ferric sulfate, ferric ammonium sulfate, ferric nitrate, ferric phosphate and ferric oxalate. The iron-chelating agent may be a compound capable of forming a chelate compound with the iron and which does not inhibit the color reaction. Such chelating agents are preferably ethylenediaminetetraacetic acid, nitrileacetic acid, 1,2-cyclohexanediaminetetraacetic acid, glycol etherdiaminetetraacetic acid, diethylenetriaminepentaacetic acid, triethanolamine, diethanolamine, diacetyl monooxime, and inorganic salts thereof (e.g. alkali metal salts). Among these compounds, it is particularly preferred to use ethylenediaminetetraacetic acid and an alkali metal salt thereof (e.g. the sodium or potassium salt). These iron-chelating agents coordinate with ferric ions along with phenylketone bodies to give a colored chelating compound which contributes greatly to the stabilization of the ferric ion. It is thus believed that clear and stable color is formed without the unwanted formation of ferric hydroxide as a precipitate. The chelating agent can also. masking various metal ions in the body fluids that undesirably affect the color reaction. As a result, a very stable color with strong intensity is formed with the color reaction.
De løsningsmidler som anvendes ved fremstillingen av impregner-ingsoppløsningen omfatter for eksempel vann, organiske løsnings-midler ( f.eks. metanol, etanol, aceton og andre med et lavt kokepunkt) og blandinger derav. Når det anvendes et vandig organisk løsningsmiddel vil reagensene gi et slikt løsnings-middel impregneres jevnt og homogent inn i det absorberende materiale og således gi en jevn farge ved farge-reaksjonen. The solvents used in the preparation of the impregnation solution include, for example, water, organic solvents (e.g. methanol, ethanol, acetone and others with a low boiling point) and mixtures thereof. When an aqueous organic solvent is used, the reagents will cause such a solvent to be impregnated evenly and homogeneously into the absorbent material and thus give a uniform color during the color reaction.
I tillegg er tørreprosessen ved fremstillingen av prøvestrim-lene i et slikt tilfelle forenklet. In addition, the drying process for the production of the test strips is simplified in such a case.
Ferrisaltet anvendes vanlig i form av en oppløsning med en konsentrasjon på 10 til 20$, og det jern-chelaterende middel kan anvendes i form av en oppløsning med en konsentrasjon på omtrent 0,1 til 10$. Den optimale konsentrasjon for begge oppløsninger er omtrent 5$ for hver. The ferric salt is usually used in the form of a solution with a concentration of 10 to 20%, and the iron chelating agent can be used in the form of a solution with a concentration of approximately 0.1 to 10%. The optimal concentration for both solutions is about 5$ for each.
Det absorberende materiale som skal dyppes ned i en oppløsning inneholdende ferrisaltet og det jern-chelaterende middel kan være et papirark, et stykke tekstil eller en trepinne. The absorbent material to be dipped into a solution containing the ferric salt and the iron-chelating agent can be a sheet of paper, a piece of textile or a wooden stick.
Typiske eksempler på papirtyper er filterpapir, trekkpapir, absorberende papir (f.eks., silica gel papir, aluminiumoksyd-papir), ioneveksler~cellulosepapir (f.eks. fosfonmetyl-cellulose papir; sulfoetyl cellulosepapir, fosfor cellulosepapir, guanidoetyl cellulosepapir, dietylaminoetyl cellulosepapir, aminoetyl cellulosepapir, ekteora cellulosepapir, p-aminobenzyl cellulosepapir, polyetylenimin cellulosepapir), ionevekslings "Sephadex"- papir, og ioneveksler harpiks-papir. Andre absorberende materiale med den samme egenskap kan like gjerne anvendes. Blant slike absorberende materialer anvendes foretrukket ioneveksler-cellulosepapirer, særlig dietylaminoetyl cellulosepapir. Formen for det absorberende materiale er ikke , spesielt begrenset, men det anvendes vanlig i strimmelform. Typical examples of paper types are filter paper, tracing paper, absorbent paper (e.g., silica gel paper, aluminum oxide paper), ion exchanger ~ cellulose paper (e.g., phosphonmethyl cellulose paper; sulfoethyl cellulose paper, phosphorous cellulose paper, guanidoethyl cellulose paper, diethylaminoethyl cellulose paper , aminoethyl cellulose paper, ectora cellulose paper, p-aminobenzyl cellulose paper, polyethyleneimine cellulose paper), ion exchange "Sephadex" paper, and ion exchange resin paper. Other absorbent material with the same properties can just as easily be used. Among such absorbent materials, ion exchange cellulose papers are preferably used, in particular diethylaminoethyl cellulose paper. The shape of the absorbent material is not particularly limited, but it is usually used in strip form.
Selve løsningen' som inneholder de aktive bestandeler kan anvendes for .å påvise fenylketon-legemer ved å tilsette den til en prøve av kroppsvæskene som for eksempel urin, plasma eller serum, hvorved det opptrer en synlig fargeendring...Fra et synspunkt med hensyn til håndtering, stabilitet og lagring til praktisk bruk, anvendes sammensetningen fordelaktig eller ±* form av et fast preparat enn i form av selve den impregnerende oppløsning. Faste preparater som for eksempel tabletter, granuler, piller eller pulvere som inneholder de nødvendige komponenter kan fremstilles på konvensjonell måte. Ved fremstillingen av slike preparater, kan egnete tilsetningsmidler (■f .eks. bære re, oppløselighets fremmende midler, dispergerende midler, bindemidler) tilsettes uten å endre grunnlaget for den foreliggende oppfinnelse. Fargeendringen kan påvises enkelt ved å oppløse dette faste preparat i kroppsvæskene som inneholder fenylketon-legmene. Fargereaksjonen kan også gjennomføres på en slik måte at en tablett som inneholder et ferrisalt og en tablett som inneholder et jern-chelaterende middel, vanlig i separate pakninger, kombineres en prøve av kroppsvæskene ved bruken. The solution itself containing the active ingredients can be used to detect phenylketone bodies by adding it to a sample of body fluids such as urine, plasma or serum, whereby a visible color change occurs...From the point of view of handling, stability and storage for practical use, the composition is advantageously used in the form of a solid preparation rather than in the form of the impregnating solution itself. Solid preparations such as tablets, granules, pills or powders containing the necessary components can be prepared in a conventional manner. In the preparation of such preparations, suitable additives (eg carriers, solubility-promoting agents, dispersing agents, binders) can be added without changing the basis of the present invention. The color change can be detected easily by dissolving this solid preparation in the body fluids containing the phenylketone bodies. The color reaction can also be carried out in such a way that a tablet containing a ferric salt and a tablet containing an iron-chelating agent, usually in separate packages, are combined a sample of the body fluids at the time of use.
Prøvestrimmelen i henhold til den foreliggende oppfinnelse anvendes vanlig ved å dyppe den ned i en prøve eller ved å impregnere en prøve inn i prøvestrimmelen, hvorved"en synlig fargeendring finner sted. Fenylketonuria kan påvises enndog ved å anvende en bleie fuktig av det nyfødte barns urin ved å bringe prøvestrimmelen i kontakt med bleien. Når plasma eller serum anvendes som prøve er den samme anvendelse mulig ved å anvende prøvestrimmelen i henhold til oppfinnelsen. Prøvestrimmelen i henhold til oppfinnelsen kan om ønsket anvendes i en mer fordelaktig form ved at deh for eksempel er fiksert på et plastark. The test strip according to the present invention is usually used by dipping it into a sample or by impregnating a sample into the test strip, whereby a visible color change takes place. Phenylketonuria can also be detected by using a diaper moistened with the newborn child's urine by bringing the test strip into contact with the diaper. When plasma or serum is used as a sample, the same application is possible by using the test strip according to the invention. The test strip according to the invention can, if desired, be used in a more advantageous form by, for example, being fixed on a plastic sheet.
De følgende utførelseseksempler skal illustrere foretrukne ut-førelsesformer for oppfinnelsen. The following exemplary embodiments shall illustrate preferred embodiments of the invention.
E ksempel 1.Example 1.
Ferriklorid (l g) og etyiendiammtetraeddiksyre (l g) ble opp-løst i vann ( 20"ml) til å gi en klar gul oppløsning; Et stykke ( 5 x 15 om)"dietylaminoetyl cellulosepapir "DE«8l" (Whatman Co.) ble dyppet ned i den overnevnte oppløsning i ett minutt Ferric chloride (1 g) and ethylenediaminetetraacetic acid (1 g) were dissolved in water (20 ml) to give a clear yellow solution; immersed in the above solution for one minute
og deretter ble overskudd av reagens fjernet fra papiret med et filterpapir. Strimmelen ble tørret i luft eller under redusert trykk, fiksert til et plastark, og kuttet opp i passende store stykker til å gi deri ønskede prøvestrimmel. and then excess reagent was removed from the paper with a filter paper. The strip was dried in air or under reduced pressure, fixed to a plastic sheet, and cut into appropriately sized pieces to provide therein the desired sample strip.
Når prøvestrimmelen ble undersøkt under anvendelser av urin-prøver inneholdende p»fenylpyrodruesyre ved en konsentrasjon av 10, 20, 50, 100 og 200 mg/100 ml, endret strimmelen farge fra klar gul til grønn-blå og til slutt blå-grønn ettersom konsentrasjonen av fenylpyrodruesyre økte. Den dannede farge på strimmelen bleknet ikke i løpet av 5 til J>Q minutter når prøven ble gjennomført ved å anvende urinprøver med en konsentrasjon på mer enn 10 mg/100 ml p-fenylpyrodruesyre. Fargen på selve prøvestrimmelen var klart gul i fravær av P-fenylpyrodruesyre. When the test strip was examined under applications of urine samples containing p»phenylpyruvic acid at a concentration of 10, 20, 50, 100 and 200 mg/100 ml, the strip changed color from clear yellow to green-blue and finally blue-green as the concentration of phenylpyruvic acid increased. The color formed on the strip did not fade within 5 to 10 minutes when the test was conducted using urine samples with a concentration of more than 10 mg/100 ml of p-phenylpyruvic acid. The color of the test strip itself was bright yellow in the absence of P-phenylpyruvic acid.
Eksempel 2Example 2
Under anvendelse av et sillca gel papir " M3F 8860" (Carl Chleicher & Chttll Co.) istedet for dietylaminoetyl '"cellulose papir, ble'den samme fremgangsmåte som beskrevet i eksemplet 1 gjennomført til å gi en prøvestrimmel for påvisning av fenylketon-legemer i urinen. Den således oppnådde prøvestrimmel hadde den samme følsomhet"overfor P-fenylpyrodruesyre som den strimmel som var oppnådd i eksempel-1. Using silica gel paper "M3F 8860" (Carl Chleicher & Chtll Co.) instead of diethylaminoethyl cellulose paper, the same procedure as described in Example 1 was carried out to provide a test strip for the detection of phenylketone bodies in the urine. The test strip thus obtained had the same sensitivity to P-phenylpyruvic acid as the strip obtained in Example-1.
Eksempel 3.Example 3.
Under.anvendelse av ferrisulfat (l g) istedet for ferriklorid, ble den samme fremgangsmåte som beskrevet i eksempel 1 gjennom-ført til å gi en fenylketonuria -prøvestrimmel. Using ferric sulfate (1 g) instead of ferric chloride, the same procedure as described in example 1 was carried out to give a phenylketonuria test strip.
Eksem pe l 4.Example 4.
Glykoleterdiamintetraeddiksyre (1,2 g) og ferriklorid (1 g) ble oppløst i vann ( 20 ml) til"å gi en klar gulaktig løsning. Et stykke (5x6 cm) av dietylaminoetyl cellulosepapir "SG-8l" Glycoletherdiaminetetraacetic acid (1.2 g) and ferric chloride (1 g) were dissolved in water (20 ml) to give a clear yellowish solution. A piece (5x6 cm) of diethylaminoethyl cellulose paper "SG-8l"
(Whatman Co.) ble dyppet i denne oppløsning og papiret tørret"i luften til"å gi en fenylketonuria-prøvestrimmel. Følsomheten for prøvestrimmelen overfor fenylketon-legemer^var den samme som for prøvestrimmelen oppnådd i eksempel 1. (Whatman Co.) was dipped in this solution and the paper dried in the air to provide a phenylketonuria test strip. The sensitivity of the test strip to phenyl ketone bodies was the same as that of the test strip obtained in Example 1.
Under anvendelse av nitrilotrieddiksyre, 1,2-syklohexandiamintetraeddiksyre, dietylentriaminpentaeddiksyre, trietanolamin og diacetylmonooxim istedet for glykoleterdiamintetraeddiksyre, ble den samme fremgangsmåte som ovenfor fulgt til å gi de til-svarende fenylketonuria-prøvestrimler. Using nitrilotriacetic acid, 1,2-cyclohexanediaminetetraacetic acid, diethylenetriaminepentaacetic acid, triethanolamine and diacetyl monooxime instead of glycol etherdiaminetetraacetic acid, the same procedure as above was followed to provide the corresponding phenylketonuria test strips.
E ksempel 5.Example 5.
Under anvendelse av filterpapir (Toyo filter paper No. ljl) istedet for dietylaminoetyl cellulosepapir ble den samme fremgangsmåte som beskrevet i eksempel 1 gjennomført til å gi en Using filter paper (Toyo filter paper No. ljl) instead of diethylaminoethyl cellulose paper, the same procedure as described in example 1 was carried out to give a
fenylketonuria-prøvestrimmel.phenylketonuria test strip.
Eksempel 6.Example 6.
Ferriklorid ( lg) og dinatriumsalt av etylendiamintetraeddiksyre (l"g) ble oppløst i en 10$ vandig etanol (20 ml), Ferric chloride (1g) and disodium salt of ethylenediaminetetraacetic acid (1g) were dissolved in a 10% aqueous ethanol (20ml),
og fremgangsmåten i eksempel 1 ble fulgt til å gi en fenyl» ketonuria-prøvestrimmel. and the procedure of Example 1 was followed to provide a phenylketonuria test strip.
E ksempel 7»E xample 7»
Under anvendelse av ferriammoniumsulfat (1,-J>. g) istedet for ferriklorid ble den samme fremgangsmåte som beskrevet i eksempel 1'gjennomført til å gi en fenylketonuria-prøvestrimmel. Using ferric ammonium sulfate (1.-J>. g) instead of ferric chloride, the same procedure as described in Example 1' was carried out to give a phenylketonuria test strip.
E ksempel 8.Example 8.
Ferriklorid (l g), etylendiamintetraeddiksyre (l g) og polyetylenglykol'4000 ( 2 g) ble oppløst i vann (20 ml) og deretter ble fremgangsmåten"fra eksempel 1 fulgt til å gi den ønskede prøvestrimmel. Ferric chloride (1g), ethylenediaminetetraacetic acid (1g) and polyethylene glycol'4000 (2g) were dissolved in water (20ml) and then the procedure from Example 1 was followed to give the desired test strip.
Claims (6)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48105291A JPS5240239B2 (en) | 1973-09-18 | 1973-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO742321L true NO742321L (en) | 1975-04-14 |
Family
ID=14403566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| NO742321A NO742321L (en) | 1973-09-18 | 1974-06-26 |
Country Status (14)
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| US (1) | US3954412A (en) |
| JP (1) | JPS5240239B2 (en) |
| BE (1) | BE816924A (en) |
| CA (1) | CA1021235A (en) |
| CH (1) | CH598595A5 (en) |
| DE (1) | DE2432752A1 (en) |
| DK (1) | DK332274A (en) |
| ES (1) | ES427746A1 (en) |
| FR (1) | FR2244174B1 (en) |
| GB (1) | GB1444294A (en) |
| IT (1) | IT1016643B (en) |
| NL (1) | NL7410508A (en) |
| NO (1) | NO742321L (en) |
| SE (1) | SE7408130L (en) |
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| FR2385377A2 (en) * | 1976-04-29 | 1978-10-27 | Inst Nat Rech Securite | METHOD OF FIXING URINARY METABOLITES ON AN ADSORBENT SUPPORT AND DEVICE FOR IMPLEMENTING THIS PROCESS |
| JPS55142249A (en) * | 1979-04-24 | 1980-11-06 | Shionogi & Co Ltd | Reduction type ascorbic acid detecting composition and test piece |
| US4288541A (en) * | 1979-10-15 | 1981-09-08 | Miles Laboratories, Inc. | Ascorbate resistant composition, test device and method for detecting a component in a liquid test sample |
| US4472507A (en) * | 1981-06-04 | 1984-09-18 | Pluim Jr Arthur W | Method for detecting exposure to poison ivy and the like |
| US5362630A (en) * | 1981-07-28 | 1994-11-08 | Duke University | Isolation of pseudomonas salicylate hydroxlase and its use for the identification and quantitation of salicylate in body fluids |
| US4397956A (en) * | 1981-12-10 | 1983-08-09 | Maggio Edward T | Means for monitoring the status of control of ketoacidosis-prone diabetics |
| US4701420A (en) * | 1985-04-01 | 1987-10-20 | Eastman Kodak Company | Analytical compositions, elements and methods utilizing reduction of ferric ion chelates to form detectable dyes |
| JPH03290443A (en) * | 1990-04-06 | 1991-12-20 | Sakai Eng Kk | Continuously foamed cellulosic molded material containing functional group having ion exchangeability |
| GB0405648D0 (en) * | 2004-03-12 | 2004-04-21 | Bloomsbury Innovations Ltd | Apparatus |
| US10330603B1 (en) * | 2016-04-08 | 2019-06-25 | Michael D. Callahan | Mass produced, low cost, portable test kit for the detection and identification of chemical and biological agents |
| US9759733B1 (en) * | 2016-04-08 | 2017-09-12 | Michael D. Callahan | Mass produced, low cost, portable test kit for the detection and identification of narcotics |
| EP3679343B1 (en) * | 2017-09-06 | 2023-06-07 | Clemson University Research Foundation | Coupon design for enhanced color sensitivity for colorimetric-based chemical analysis of liquids |
| CN110441524A (en) * | 2019-07-22 | 2019-11-12 | 浙江大学 | Detect application of the antibody of phenylketonuria marker in preparation diagnosis test paper |
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| NL238977A (en) * | 1958-06-16 | |||
| GB1050880A (en) * | 1964-11-13 | |||
| US3537906A (en) * | 1966-01-05 | 1970-11-03 | Allis Chalmers Mfg Co | Process for producing a fuel cell electrode |
| US3511611A (en) * | 1968-01-23 | 1970-05-12 | Pfizer & Co C | Blood urea nitrogen test |
-
1973
- 1973-09-18 JP JP48105291A patent/JPS5240239B2/ja not_active Expired
-
1974
- 1974-06-17 US US05/480,308 patent/US3954412A/en not_active Expired - Lifetime
- 1974-06-19 SE SE7408130A patent/SE7408130L/xx unknown
- 1974-06-20 DK DK332274A patent/DK332274A/da unknown
- 1974-06-25 CA CA203,372A patent/CA1021235A/en not_active Expired
- 1974-06-26 NO NO742321A patent/NO742321L/no unknown
- 1974-06-26 BE BE145944A patent/BE816924A/en unknown
- 1974-06-27 ES ES427746A patent/ES427746A1/en not_active Expired
- 1974-06-28 FR FR7422699A patent/FR2244174B1/fr not_active Expired
- 1974-07-08 DE DE2432752A patent/DE2432752A1/en not_active Withdrawn
- 1974-07-10 GB GB3058374A patent/GB1444294A/en not_active Expired
- 1974-07-19 IT IT69309/74A patent/IT1016643B/en active
- 1974-07-19 CH CH1000474A patent/CH598595A5/xx not_active IP Right Cessation
- 1974-08-05 NL NL7410508A patent/NL7410508A/en unknown
Also Published As
| Publication number | Publication date |
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| US3954412A (en) | 1976-05-04 |
| FR2244174A1 (en) | 1975-04-11 |
| JPS5240239B2 (en) | 1977-10-11 |
| ES427746A1 (en) | 1977-02-01 |
| CH598595A5 (en) | 1978-05-12 |
| FR2244174B1 (en) | 1978-01-27 |
| CA1021235A (en) | 1977-11-22 |
| NL7410508A (en) | 1975-03-20 |
| GB1444294A (en) | 1976-07-28 |
| BE816924A (en) | 1974-10-16 |
| DE2432752A1 (en) | 1975-04-03 |
| JPS5057300A (en) | 1975-05-19 |
| DK332274A (en) | 1975-06-02 |
| IT1016643B (en) | 1977-06-20 |
| SE7408130L (en) | 1975-03-19 |
| AU7053274A (en) | 1976-01-08 |
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